Hydrazine → 5-Hydroxy-6-methoxy-2H-phthalazin-1-one

HRID 2268870Notes

Reaction equation

HRID 2268870 reaction equation
O[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:12][CH3:13])[C:9]=2[OH:11])[C:4](=O)[O:3]1.[NH2:15][NH2:16]>C(O)C>[OH:11][C:9]1[C:8]([O:12][CH3:13])=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:2]=[N:15][NH:16][C:4]2=[O:3]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 185047873,4-Dihydroxy-5-methoxy-3H-isobenzofuran-1-one

Product 1

HCID 1355563055-Hydroxy-6-methoxy-2H-phthalazin-1-oneYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3,4-dihydroxy-5-methoxy-3H-isobenzofuran-1-one (6.63 g, 34 mmoles), prepared as described in example 57, in ethanol (60 ml) was added with 98% hydrazine (8.5 ml). The mixture was heated to clarity and after 5 minutes a precipitate formed and was filtered and treated with 1N HCl. The mother liquors were concentrated more times and the resultant solid fractions joined to give 4.65 g of the title compound (yield: 72%).

Workup

  1. temperatureThe mixture was heated to clarity and after 5 minutes a precipitate
  2. customformed
  3. filtrationwas filtered
  4. additiontreated with 1N HCl
  5. concentrationThe mother liquors were concentrated more times

Sources & evidence

ORD record
ord-1c23218d74444ff2bec4f8863656d5e1
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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